(-)-(S)-8-phenyl-1-[(E)-phenylprop-2-enoyl]-1,5,9,13-tetraazacycloheptadecan-6-one | 164230-52-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (-)-(S)-8-phenyl-1-[(E)-phenylprop-2-enoyl]-1,5,9,13-tetraazacycloheptadecan-6-one
• 英文别名: (-)(S)-verbacine；(S)-verbacine；Verbacine；(-)-(S)-verbacine；(8S)-8-phenyl-1-[(E)-3-phenylprop-2-enoyl]-1,5,9,13-tetrazacycloheptadecan-6-one
• CAS: 164230-52-8
• 化学式: C₂₈H₃₈N₄O₂
• 分子量: 462.635
• InChiKey: ASBBGSDFHKCHMP-OXVFXORMSA-N

物化性质

• 沸点：
  723.4±60.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  73.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(S)-8-phenyl-1-[(E)-phenylprop-2-enoyl]-1,5,9,13-tetraazacycloheptadecan-6-one 在 palladium on activated charcoal 氢气 、 sodium phosphate 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.5h， 生成 (-)-dihydroverbaskine
  参考文献：
  名称：

  Verbacine和verballocine，来自Verbascum pseudonobile Stoj的新型大环精胺生物碱。et Stef。（玄参科）

  摘要：

  据报道，含有精胺，E-（或Z-）肉桂酰基和苯基丙酰基前体单元的新型17元内酰胺生物碱verbacine（1）和verballocine（2）的分离和结构解析。提供了以前报道的维拉巴辛的人工来源的证据。

  DOI：

  10.1016/0040-4039(94)02317-5
• 作为产物：
  描述：

  (+)-(2S)-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one 在 盐酸羟胺 、 三乙胺 作用下， 以 盐酸 、 二氯甲烷 为溶剂， 生成 (-)-(S)-8-phenyl-1-[(E)-phenylprop-2-enoyl]-1,5,9,13-tetraazacycloheptadecan-6-one
  参考文献：
  名称：

  Asymmetric Syntheses of the Macrocyclic Spermine Alkaloids (−)-(S)-Protoverbine, (−)-(S)-Buchnerine, and Their Naturally Occurring Congenial Alkaloids

  摘要：

  Asymmetric syntheses of the following 17-membered macrocyclic spermine alkaloids are presented: (-)-(S)-protoverbine (= (8S)-8-phenyl-1,5,9,13-tetraazacycloheptadecane-6-one; 1), (+)-(S)-protomethine (=(2S)-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one; 2), (-)-(S)-buchnerine (=(8S)-8-(4-methoxyphenyl)-1,5,9,13-tetraazacycloheptadecane-6-one; 8), (+)-(S)-VeTbamethine (=(-')-(2S)-9-[(E)-phenylprop- 2-enoyl]-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one; 4), (-)-(S)-verbacine [(E)-phenylprop-2-enoyl]-8-phenyl-1,5,9,13-tetraazacycloheptadecan-6-one; 3), (-)-(S)-verbasikrine (8S)-1-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-8-phenyl-1,5,9,13-tetraazacycloheptadecan-6-one; 26), (S)-isoverbasikrine (=(-)-(8S)-1-[(Z)-3-(4-methoxyphenyl)prop-2-enoyl]-8-phenyl-1,5,9,13-tetraazacycloheptadecan-6-one; 25), (+)-(S)-verbamekrine (= (+)-(2S)-9-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-2-phenyl- 1,5,9.14-tetraazabicyclo[12.3.1]octadecan-4- one; 23), and(+)-(S)-isoverbamekrine (=(+)-(2S)-9-[(Z)-3-(4-methoxyphenyl)prop-2-enoyl]-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one; 24). Effective methods for H-1-NMR determination of the enantiomeric purity in which (S)-2-hydroxy-2-phenylacetic acid and (S)-2-acetoxy-2-phenylacetic acid are used as shift reagents for 1, 8, and related macrocyclic alkaloids are described.

  DOI：

  10.1002/1522-2675(200204)85:4<979::aid-hlca979>3.0.co;2-f

文献信息

• C 1 -Derivatives of macrocyclic spermine alkaloids. Verbamedines versus incasines
  作者：Konstantin Drandarov、Manfred Hesse

  DOI：10.1016/s0040-4039(02)01020-1

  日期：2002.7

  structure elucidation, and synthesis of the macrocyclic spermine alkaloids verbamedine (3) and isoverbamedine (4) from Verbascum pseudonobile Stoj. and Stef. are reported. The synthesis of N(13)-formimino-verbacine (7) is described. Spectral and chemical evidence is presented to correct the previously published incorrect structures of the incasines A and A′ isolated from Incarvillea sinensis LAM. The similarities

  隔离，结构鉴定，和大环精胺生物碱合成verbamedine（3）和isoverbamedine（4从）毛蕊花pseudonobile Stoj。和Stef。被报道。描述了N（13）-甲亚氨基-verbacine（7）的合成。提出了光谱和化学证据来纠正先前发表的从中华Incarvillea sinensis LAM分离的Incasines A和A'的不正确结构。观察到了天然的Verbacine（1）C 1衍生物与转移四氢叶酸辅因子的生化一碳单元之间的相似性。
• Asymmetric Syntheses of the Macrocyclic Spermine Alkaloids (−)-(S)-Protoverbine, (−)-(S)-Buchnerine, and Their Naturally Occurring Congenial Alkaloids
  作者：Konstantin Drandarov、Armin Guggisberg、Manfred Hesse

  DOI：10.1002/1522-2675(200204)85:4<979::aid-hlca979>3.0.co;2-f

  日期：2002.4

  Asymmetric syntheses of the following 17-membered macrocyclic spermine alkaloids are presented: (-)-(S)-protoverbine (= (8S)-8-phenyl-1,5,9,13-tetraazacycloheptadecane-6-one; 1), (+)-(S)-protomethine (=(2S)-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one; 2), (-)-(S)-buchnerine (=(8S)-8-(4-methoxyphenyl)-1,5,9,13-tetraazacycloheptadecane-6-one; 8), (+)-(S)-VeTbamethine (=(-')-(2S)-9-[(E)-phenylprop- 2-enoyl]-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one; 4), (-)-(S)-verbacine [(E)-phenylprop-2-enoyl]-8-phenyl-1,5,9,13-tetraazacycloheptadecan-6-one; 3), (-)-(S)-verbasikrine (8S)-1-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-8-phenyl-1,5,9,13-tetraazacycloheptadecan-6-one; 26), (S)-isoverbasikrine (=(-)-(8S)-1-[(Z)-3-(4-methoxyphenyl)prop-2-enoyl]-8-phenyl-1,5,9,13-tetraazacycloheptadecan-6-one; 25), (+)-(S)-verbamekrine (= (+)-(2S)-9-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-2-phenyl- 1,5,9.14-tetraazabicyclo[12.3.1]octadecan-4- one; 23), and(+)-(S)-isoverbamekrine (=(+)-(2S)-9-[(Z)-3-(4-methoxyphenyl)prop-2-enoyl]-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one; 24). Effective methods for H-1-NMR determination of the enantiomeric purity in which (S)-2-hydroxy-2-phenylacetic acid and (S)-2-acetoxy-2-phenylacetic acid are used as shift reagents for 1, 8, and related macrocyclic alkaloids are described.
• Verbacine and verballocine, novel macrocyclic spermine alkaloids from Verbascum pseudonobile Stoj. et Stef. (Scrophulariaceae)
  作者：Konstantin Drandarov

  DOI：10.1016/0040-4039(94)02317-5

  日期：1995.1

  The isolation and structural elucidation of the novel 17-membered lactam alkaloids verbacine (1) and verballocine (2) containing spermine, E- (or Z-) cinnamoyl and phenylpropionyl precursory units, is reported. Evidence for the artificial origin of the previously reported verbaskine is presented.

  据报道，含有精胺，E-（或Z-）肉桂酰基和苯基丙酰基前体单元的新型17元内酰胺生物碱verbacine（1）和verballocine（2）的分离和结构解析。提供了以前报道的维拉巴辛的人工来源的证据。